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Sodium Bicarbonate → (2R)-N-{[5-bromo-1-(3-methoxypropyl)indol-3-yl]methyl}-N-cyclopropylmorpholin-2-carboxamide

HRID 872006
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HRID 872006 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:6]=[C:5]2[CH2:16][N:17]([CH:33]1[CH2:35][CH2:34]1)[C:18]([C@@H:20]1[O:25][CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21]1)=[O:19].C(=O)(O)[O-].[Na+]>ClCCCl.[Br-].[Zn+2].[Br-]>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:6]=[C:5]2[CH2:16][N:17]([CH:33]1[CH2:35][CH2:34]1)[C:18]([C@@H:20]1[O:25][CH2:24][CH2:23][NH:22][CH2:21]1)=[O:19]
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참가 물질

5

반응물 2

HCID 516892Sodium BicarbonateHCID 59494589HCID 59494589, 화합물

생성물 1

HCID 59494802(2R)-N-{[5-bromo-1-(3-methoxypropyl)indol-3-yl]methyl}-N-cyclopropylmorpholin-2-carboxamide

시약·촉매·용매 2

HCID 10421208Zinc bromide촉매HCID 111,2-Dichloroethane용매

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온도
40 °C

실험 절차

Zinc bromide (209 mg) was added to a solution of tert-butyl(2R)-2-{[{[5-bromo-1-(3-methoxypropyl)indol-3-yl]methyl}(cyclopropyl)amino]carbonyl}morpholin-4-carboxylate (a compound of Reference Example 128, 200 mg) in 1,2-dichloroethane (12 ml) and the mixture was stirred at 40° C. for 3 hours. The reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate and extracted with chloroform. The organic layer was washed with water and saturated brine, dried over magnesium sulfate and concentrated in vacuo. The resulted residue was purified with a silica gel column chromatography (eluting solvent: chloroform/methanol=98/2 to 93/7) to give (2R)—N-{[5-bromo-1-(3-methoxypropyl)indol-3-yl]methyl}-N-cyclopropylmorpholin-2-carboxamide (117 mg) as a colorless oil.

후처리

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulted residue was purified with a silica gel column chromatography (eluting solvent: chloroform/methanol=98/2 to 93/7)

출처 및 근거

ORD 기록
ord-2da09ada2c9140af8df81b64e5c246cb
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08975252B2

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